Since these teams had obviously never met before, there was a little feeling out of the style of play of each team for the first few minutes, with the home side having to adjust to the taller and stronger Coventry City side, and the visitors having to adjust to a quick Portland squad. It would be the Timbers who would have the first good scoring chance, when in the fifth minute, on a cross from Hugo Alcaraz-Cuellar to the foot of Jaime Ambriz, with the Timbers forward attempting to chip Coventry City goalkeeper Andy Marshall, but putting the shot a few yards wide to the right.

Three minutes later, the visitors would make their first good scoring opportunity of the match count when Dele Adebola headed the ball to Jay Tabb near the penalty spot in the Timbers box, and Tabb finished easily to the right side of the goal to give the Sky Blues an early 1-0 lead.

Ambriz (who has yet to play a game for the Timbers, who are still waiting for international clearance) had another good chance in the 20th minute, with his shot from 20 yards out going just a yard or two wide left. Eight minutes later, it would be the visitors with another good chance of their own, with Gary McSheffrey putting a shot just over the bar from 22 yards out.

Ten minutes later, Coventry City would get another good look at goal when McSheffey's header was right at Timbers goalkeeper Josh Saunders, who controlled the close-range header. Near the end of the first half, the Sky Blues had another good chance when Tabb made a run to the top of the Timbers box and was momentarily open, but his hard low shot was smothered by Saunders, and the half would end with Coventry City holding a 1-0 lead.

Nine minutes into the second half, the Timbers had an excellent chance to level the score when a passing sequence of Josh Brown, to Tom Poltl, to Ambriz had the Timbers striker with a quick shot from near the spot that slid just past the right post. Three minutes later, it was Ambriz again causing havoc in front of the Coventry City box, barely getting a foot onto a bouncing ball into the net, forcing Marshall to make a point-blank save, though the shot had little pace on it.

Three minutes later, Coventry City had their first good chance of the half when second half substitute Colin Cameron's low shot from 20 yards out forced a save from Timbers goalkeeper Bayard Elfvin, who had also come in at halftime.

In the 67th minute, on a Timbers corner kick, a low driven cross was attempted to be cleared by defender Andrew Thornton, who accidentally kicked the ball up and off his own arm, and referee Yader Reyes pointed to the spot as the Timbers were awarded a penalty kick. Alcaraz-Cuellar calmly buried the shot into the right side of the net, with Marshall going the wrong way, and the Timbers had leveled the score at 1-1.

In the 86th minute, with the Timbers already looking like momentum had swung their way since the penalty, the visitors would be forced even more onto their heels when Cameron was ejected, possibly for dissent. The Timbers very nearly made the advantage pay off just before stoppage time when defender Mike Randolph's overlap on the left side had him making a dangerous diagonal run into the box, but his hard shot to the near post was saved brilliantly by a reaction save by Marshall, and was probably the best save of the match.

Though the match ended 1-1 after ninety minutes, it had already been decided beforehand that any draw would be decided by penalty kicks. So after a five minute break, Coventry City would kick first.

For the first three shots, each team would be successful on all three kicks, though the first Coventry City kick would go in off the crossbar.

The fourth kick taker for Coventry City was David McNamee, and his shot would hit off the crossbar and rebound back out for the miss. Byron Alvarez slotted home the next kick for the Timbers, putting the pressure on Coventry City's Claus Jorgensen. The English midfielder did not even put the shot on goal, hitting the shot wide past the right post, with the Timbers now having Martin Hutton in goal (seeing his first Timbers action), and with the miss, the Timbers had taken the victory in PK's by a 4-3 result.

The crowd of 10,095 is the fifth largest crowd to see a home Timbers game since the team returned in 2001. The record for one match is 15,376 who watched the Timbers draw 0-0 with Sunderland AFC on July 23, 2005.